A growing number of people keep working after retirement, a phenomenon known as bridge employment. Sleep features, which are related to morbidity and mortality outcomes, are expected to be influenced by bridge employment or permanent retirement. The objective of this study was to analyze sleep duration and quality of bridge employees and permanent retirees compared to nonretired, i.e., active workers, from the Brazilian Longitudinal Study of Adult Health (ELSA-Brasil). Participants (second wave of ELSA-Brasil, 2012–2014) comprised permanently retired (n = 2348), career bridge workers (n = 694), bridge workers in a different place (n = 760), and active workers (n = 6271). The associations of all studied retirement schemes and self-reported sleep quality and duration were estimated through logistic and linear regression analysis. Workers from all studied retirement schemes showed better sleep patterns than active workers. In comparison to active workers, bridge workers who had changed workplace also showed a reduced chance of difficulty falling asleep and too-early awakenings, which were not found among career bridge workers. Bridge employment and permanent retirement were associated with a reduced chance of reporting sleep deficit. Bridge work at a different place rather than staying at the same workplace seems to be favorable for sleep. Further study is needed to explain mechanisms.